771-60-8

Basic information

• Product Name: 2,3,4,5,6-Pentafluoroaniline
• Synonyms: Aminopentafluorobenzene;Aniline, 2,3,4,5,6-pentafluoro-;Pentafluorophenylamine;PENTAFLUOROANILINE;PENTAFLUORANILINE;2,3,4,5,6-PENTAFLUOROBENZENAMINE;2,3,4,5,6-PENTAFLUOROANILINE;pentafluronitrobenzene
• CAS NO: 771-60-8
• Molecular Formula: C₆H₂F₅N
• Molecular Weight: 183.08
• EINECS: 212-234-2
• Product Categories: Aniline;Fluorobenzene;Amines;C2 to C6;Nitrogen Compounds;organofluorine compounds
• Mol File: 771-60-8.mol
• Article Data: 27

Chemical Properties

• Melting Point: 33-35 °C(lit.)
• Boiling Point: 153 °C(lit.)
• Flash Point: 165 °F
• Appearance: White to salmon/Crystalline Low Melting Solid
• Density: 1,744 g/cm3
• Vapor Pressure: 3.69mmHg at 25°C
• Refractive Index: 1.429
• Storage Temp.: Store below +30°C.
• Solubility: toluene: soluble
• PKA: -0.16±0.10(Predicted)
• Water Solubility: Soluble in toluene, and organic solvents. Insoluble in water.
• BRN: 1819387
• CAS DataBase Reference: 2,3,4,5,6-Pentafluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5,6-Pentafluoroaniline(771-60-8)
• EPA Substance Registry System: 2,3,4,5,6-Pentafluoroaniline(771-60-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• RTECS: BY7920000
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 771-60-8(Hazardous Substances Data)

Usage

Description

2,3,4,5,6-Pentafluoroaniline is a white to salmon-colored crystalline low melting solid that forms metal-drug complexes and is utilized in the preparation of various chemical compounds and catalysts.

Uses

Used in Catalyst Preparation:
2,3,4,5,6-Pentafluoroaniline is used as a precursor for the preparation of pentafluorophenylammonium triflate, an efficient catalyst for esterification and thioesterification processes. Its unique chemical properties make it a valuable component in these reactions.
Used in Synthesis of Titanium Complexes:
In the field of coordination chemistry, 2,3,4,5,6-pentafluoroaniline is used in the synthesis of various titanium complexes with two anionic [N, O-] bidentate salicylaldiminato ligands. These complexes have potential applications in various industrial processes.
Used in Pharmaceutical Applications:
2,3,4,5,6-Pentafluoroaniline forms metal-drug complexes, such as cis-Pt-(2,3,4,5,6-pentafluoroaniline)2-Br2, which have been tested against the promastigote forms of Leishmania donovani, a parasite responsible for leishmaniasis. This indicates its potential use in the development of new drugs to combat this disease.

Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of Fí and NOx.

InChI:InChI=1/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H

Upstream product

• 82-45-1 1-amino-9,10-anthracenedione 
• 80600-73-3 C₆F₅NH^(1-)*Na⁽¹⁺⁾=C₆F₅NHNa 
• 1423-15-0 perfluorophenyl azide 
• 108-88-3 toluene 
• 137124-26-6 2-Pentafluorophenylamino-3-phenyl-cycloprop-2-enone 
• 828-73-9 pentafluorophenyl hydrazine 
• 880-78-4 pentafluoronitrobenzen 
• 1801-15-6 2-(2,3,4,5,6-pentafluoro-anilino)-ethanol 
• 3299-67-0 Pentafluoroanilinobordibromid 
• 30807-79-5 C₆HBCl₂F₅N 
• 80684-61-3 N-benzyloxy-F-benzamide 
• 2251-50-5 pentafluorobenzoylchloride 
• 64317-34-6 N-(pentafluorophenyl)carbonimidoyl dichloride 
• 65-85-0 benzoic acid 

Downstream Products

• 64317-34-6 N-(pentafluorophenyl)carbonimidoyl dichloride 
• 58751-08-9 2,3,4,5,6-pentafluoroformanilide 
• 114564-99-7 Dibrom-N-(pentafluorphenyl)methanimin 
• 653-22-5 1-Acetylamino-2,3,4,5,6-pentafluorobenzen 
• 26672-01-5 N-(salicylidene)-2,3,4,5,6-pentafluoroaniline 
• 87228-28-2 N-(pentafluorophenyl)-benzimidoyl chloride 
• 1198-64-7 2,3,5,6-tetrafluorobenzene-1,4-diamine 
• 1198-63-6 2,4,5,6-tetrafluorobenzene-1,3-diamine 
• 447454-15-1 8-(pentafluoroaniline)-3,7-dimethyl-1-acetoxyl-2,6-octadiene 
• 717133-92-1 cyano-acetic acid 2-[ethyl-(4-pentafluorophenylazo-phenyl)-amino]-ethyl ester 
• 447454-22-0 8-(pentafluoroaniline)-3,7-dimethyl-1-chloro-2,6-octadiene 
• 447454-19-5 8-(pentafluoroaniline)-3,7-dimethyl-2,6-octadien-1-ol 
• 677300-30-0 1-(1-pentafluorophenyl-1H-pyrrole-2-yl)-propan-1-one 

Relevant articles and documents

Observation of an isolated intermediate of the nucleophilic aromatic substition reaction by infrared spectroscopy

(Figure Presented) Caught in the act: The σ complex formed as an intermediate in a nucleophilic aromatic substitution has been observed experimentally. Efficient direct ionization of C6F6 by coherent vacuum ultraviolet light was employed to effect the formation of C 6F5NH2 + from C6F 6 +/NH3. Comparison of the IR spectrum of (C6F6-NH3)+ with that predicted from DFT calculations showed that the cluster cation forms a stable σ complex (see picture).

Biorenewable carbon-supported Ru catalyst for: N -alkylation of amines with alcohols and selective hydrogenation of nitroarenes

Herein, we developed a renewable carbon-supported Ru catalyst (Ru/PNC-700), which was facilely prepared via simple impregnation followed by the pyrolysis process. The prepared Ru/PNC-700 catalyst demonstrated remarkable catalytic activity in terms of conversion and selectivity towards N-alkylation of anilines with benzyl alcohol and chemoselective hydrogenation of aromatic nitro compounds. In addition, local anesthetic pharmaceutical agents (e.g., butamben and benzocaine), including key drug intermediates, were synthesized in excellent yields under mild conditions and in the presence of water as a green solvent. Moreover, the prepared Ru/PNC-700 catalyst could be easily recovered and reused up to five times without any apparent loss in activity and selectivity.

Coordination or Oxidative Addition? Activation of N-H with [Tp′Rh(PMe3)]

A thermal reaction of amines, anilines, and amides with Tp′Rh(PMe3)(CH3)H (1, Tp′ = tris(3,5-dimethyl-pyrazolyl)borate) is described in this report. No N-H bond cleavage was observed for reactions between ammonia or unsubstituted aliphatic amines with the reactive fragment [Tp′Rh(PMe3)]. Instead, amine coordination products (κ2-Tp′)Rh(PMe3)(NHR1R2) (R1 = H, R2 = H, nPr, iPr, octyl; R1 = R2 = Et; R1, R2: pyrrolidine) were observed, and the crystal structure of (κ2-Tp′)Rh(PMe3)(NH2iPr) is reported. No coordination products were observed when 1 was reacted with 1,1,1,3,3,3-hexafluoropropan-2-amine, anilines, and amides. Instead, the oxidative addition products (κ3-Tp′)Rh(PMe3)(NHR)H (R = CH(CF3)2, C6H5, 3,5-dimethylbenzyl, C6F5, C(O)CH3, C(O)CF3) were observed. Both RhI-N coordination products (κ2-Tp′)Rh(PMe3)(NH2CH2CF3) and RhIII N-H addition products (κ3-Tp′)Rh(PMe3)(NHCH2CF3)H were generated when 1 was reacted with 2,2,2-trifluoroethylamine. Coordination products dissociate ammonia and amines in benzene much faster than oxidative addition products eliminate anilines and amides. The relative metal-nitrogen bond energies were studied using established kinetic techniques. Analysis of the relationship between the relative M-N bond strengths and N-H bond strengths showed a linear correlation with a slope = RM-N/N-H of 0.91 (10), indicating that the Rh-N bond strength varies in direct proportion to the N-H bond strength.